JP6476134B2 - 透明フレキシブルハードコーティングフィルム及びその製造方法 - Google Patents
透明フレキシブルハードコーティングフィルム及びその製造方法 Download PDFInfo
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- JP6476134B2 JP6476134B2 JP2015557940A JP2015557940A JP6476134B2 JP 6476134 B2 JP6476134 B2 JP 6476134B2 JP 2015557940 A JP2015557940 A JP 2015557940A JP 2015557940 A JP2015557940 A JP 2015557940A JP 6476134 B2 JP6476134 B2 JP 6476134B2
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- PXRMLPZQBFWPCV-UHFFFAOYSA-N dioxasilirane Chemical compound O1O[SiH2]1 PXRMLPZQBFWPCV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GLQOFBCJADYRKR-UHFFFAOYSA-K erbium(3+);trifluoromethanesulfonate Chemical compound [Er+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F GLQOFBCJADYRKR-UHFFFAOYSA-K 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- WGJJZRVGLPOKQT-UHFFFAOYSA-K lanthanum(3+);trifluoromethanesulfonate Chemical compound [La+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WGJJZRVGLPOKQT-UHFFFAOYSA-K 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DSQCNXSPLHDLED-UHFFFAOYSA-M methanesulfonate;tetrabutylphosphanium Chemical compound CS([O-])(=O)=O.CCCC[P+](CCCC)(CCCC)CCCC DSQCNXSPLHDLED-UHFFFAOYSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QMLWSAXEQSBAAQ-UHFFFAOYSA-N oxetan-3-ol Chemical compound OC1COC1 QMLWSAXEQSBAAQ-UHFFFAOYSA-N 0.000 description 1
- 239000011224 oxide ceramic Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- DDCWGUIPLGMBPO-UHFFFAOYSA-K samarium(3+);trifluoromethanesulfonate Chemical compound [Sm+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F DDCWGUIPLGMBPO-UHFFFAOYSA-K 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
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- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
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Description
(R1SiO3/2)a(R2 2SiO2/2)b(R3 3SiO1/2)c(SiO4/2)d(R4O1/2)e;
R1、R2、及びR3は、それぞれ独立に、置換可能なC1−20アルキル基、置換可能なC2−20アルケニル基、置換可能なC2−20アルキニル基、及び置換可能なC6−20アリール基からなる群より選択されるものであるが、但し、前記R1、R2、及びR3のうち平均1種以上は、脂環式エポキシ基であり、
aは、正数であり、
bは、0または正数であり、
cは、0または正数であり、
dは、0または正数であり、
eは、0または正数であり、
(b+c+d)/aは、0〜1の範囲の数であり、
e/(a+b+c+d)は、0〜0.4の範囲の数である。
成分(A):(CESiO3/2)1(MeO1/2)0.05;
成分(B):(3,4−エポキシシクロヘキシル)メチル3,4−エポキシシクロヘキシルカルボキシレート;及び、
成分(C):トリアリールスルホニウムヘキサフルオロアンチモン酸塩。
成分(A):(CESiO3/2)0.9(MCSiO3/2)0.1(MeO1/2)0.04;
成分(B):(3,4−エポキシシクロヘキシル)メチル3,4−エポキシシクロヘキシルカルボキシレート;及び、
成分(C):トリアリールスルホニウムヘキサフルオロアンチモン酸塩。
成分(A):(CESiO3/2)0.8(Ph2SiO2/2)0.2(MeO1/2)0.04;
成分(B):(3,4−エポキシシクロヘキシル)メチル3,4−エポキシシクロヘキシルカルボキシレート;及び、
成分(C):トリアリールスルホニウムヘキサフルオロアンチモン酸塩。
成分(A):(CESiO3/2)1(MeO1/2)0.05;
成分(B):3−エチル−3[(3−エチルオキセタン−3−イル)メトキシ]メチルオキセタン;及び、
成分(C):トリアリールスルホニウムヘキサフルオロアンチモン酸塩。
成分(A):(CESiO3/2)1(MeO1/2)0.05;
成分(B):4−((3−エチルオキセタン−3−イル)メトキシ)ブタン−1−オール;及び、
成分(C):トリアリールスルホニウムヘキサフルオロアンチモン酸塩。
成分(A):(CESiO3/2)1(MeO1/2)0.05;
成分(B):(3,4−エポキシシクロヘキシル)メチル3,4−エポキシシクロヘキシルカルボキシレート;及び、
成分(C):1−(3−メチルブタ−2−エニル)テトラヒドロ−1H−チオフェニウムヘキサフルオロアンチモン酸塩。
本実施例により製造された透明フレキシブルハードコーティングフィルムの表面硬度を測定するために、ASTM D3363による鉛筆硬度計を用い、その結果を下記の表1に示した。
本実施例により製造された透明フレキシブルハードコーティングフィルムの柔軟性を評価するために、屈曲半径10mmの屈曲試験(bending test)をハードコーティング層を内側にして1,000回繰り返し、これによるクラック(crack)発生有無により通過有無を確認し、その結果を下記の表1に○(クラックの発生無し)、X(クラックの発生有り)で示した。
本実施例により製造された透明フレキシブルハードコーティングフィルムの耐スクラッチ性を評価するために、#0000のスチールウォールを用いて2.45N/cm2の荷重でハードコーティングフィルムの表面を300回繰り返して擦り、これによるスクラッチ発生有無により通過有無を確認し、その結果を下記の表1に○(スクラッチの発生無し)、X(スクラッチの発生有り)で示した。
Claims (5)
- 基材フィルムと、分子1個当たり平均1種以上の脂環式エポキシ基を含むオリゴシロキサン[成分(A)];任意要素の分子1個当たり平均1種以上の脂環式エポキシ基または平均1種以上のオキセタン基を含む反応性希釈剤[成分(B)];及び、イオン重合開始剤[成分(C)]を含むイオン重合性シロキサンハードコーティング組成物を重合することによって、前記基材フィルム上に形成されたコーティング層と、を有し、
前記成分(A)が下記の化学式1で表される平均単位化学式を有するものであり、
前記成分(B)を追加に含む場合、前記成分(A)100重量部に対して5重量部〜50重量部の前記成分(B)を含むものであり、
前記成分(A)100重量部または前記成分(A)及び前記成分(B)の混合物100重量部に対して0.1重量部〜10重量部の前記成分(C)を含むものである、
[化学式1]
(R1SiO3/2)a(R2 2SiO2/2)b(R3 3SiO1/2)c(SiO4/2)d(R4O1/2)e;
前記化学式1において、
R1は、脂環式エポキシ基であり、R2及びR3は、それぞれ独立に、置換可能なC1−20アルキル基、置換可能なC2−20アルケニル基、置換可能なC2−20アルキニル基、及び置換可能なC6−20アリール基、脂環式エポキシ基からなる群より選択されるものであり、
前記R2及びR3に置換可能な置換基は、C1−20アルキル基、C3−8シクロアルキル基、C1−20アルコキシ基、アミノ基、アクリル基、メタクリル基、ハロゲン、アリル基、メルカプト基、エーテル基、エステル基、カルボニル基、カルボキシル基、ビニル基、ニトロ基、スルホン基、ヒドロキシ基、シクロブテン基、アルキド基、ウレタン基、オキセタン基、フェニル基及びこれらの組み合わせからなる群より選択される1種以上であり、
R4は、線状または分枝状のC1−7アルキル基または水素であり、
aは、正数であり、
bは、0または正数であり、
cは、0または正数であり、
dは、0または正数であり、
eは、0または正数であり、
(b+c+d)/aは、0≦(b+c+d)/a≦0.25の範囲であり、
e/(a+b+c+d)は、0〜0.4の範囲の数である、
透明フレキシブルハードコーティングフィルム。 - 前記成分(C)が陽イオン重合開始剤または陰イオン重合開始剤を含むものである、請求項1に記載の透明フレキシブルハードコーティングフィルム。
- 基材フィルム上に、請求項1又は2に記載のイオン重合性シロキサンハードコーティング組成物をコーティングし;及び、
前記イオン重合性シロキサンハードコーティング組成物のコーティング層を重合すること
を含む、
請求項1または請求項2に記載の透明フレキシブルハードコーティングフィルムの製造方法。 - 前記基材フィルムがアクリル系樹脂、スチレン系樹脂、アクリロニトリルブタジエンスチレン系樹脂、スチレンアクリロニトリル系樹脂、ポリプロピレン系樹脂、ポリエチレン系樹脂、ポリアセタール系樹脂、ポリカーボネート系樹脂、ポリアミド系樹脂、ポリ塩化ビニル系樹脂、ポリエステル系樹脂、ポリウレタン系樹脂、ノルボルネン系樹脂、シクロオレフィン系樹脂、エポキシ系樹脂、及びエーテルスルホン系樹脂からなる群より選択される1種以上の樹脂を主成分として含むものである、請求項3に記載の透明フレキシブルハードコーティングフィルムの製造方法。
- 前記重合は、光照射または熱処理により行われることである、請求項3に記載の透明フレキシブルハードコーティングフィルムの製造方法。
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